Water → HCID 118161832, compound

HRID 1050734Notes

Reaction equation

HRID 1050734 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[OH:33])[CH:10]1[CH2:19][CH2:18][CH2:17][C:16]2[CH:15]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:13]=[CH:12][C:11]1=2)[CH3:2].[C:35]([C:39]1[CH:46]=[CH:45][C:42]([CH2:43]Br)=[CH:41][CH:40]=1)([CH3:38])([CH3:37])[CH3:36].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.C(O)=O>[C:35]([C:39]1[CH:40]=[CH:41][C:42]([CH2:43][O:33][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH2:26][CH2:25][N:9]([CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:34])[CH:10]2[CH2:19][CH2:18][CH2:17][C:16]3[CH:15]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:13]=[CH:12][C:11]2=3)=[CH:45][CH:46]=1)([CH3:38])([CH3:36])[CH3:37]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 118179072HCID 118179072, compound

Product 1

HCID 118161832HCID 118161832, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

500 mg (1.07 mmol) of the compound from Example 4A were dissolved in 20 ml of DMF, 245 μl (1.23 mmol) of 4-tert-butylbenzyl bromide and 1.12 g (3.4 mmol) of caesium carbonate were added and the mixture was stirred at RT overnight. Water was then added to the mixture. After addition of 1.4 ml of 5 N formic acid, the mixture was extracted repeatedly with toluene and the combined organic phases were dried over sodium sulphate and concentrated.

Workup

  1. extractionthe mixture was extracted repeatedly with toluene
  2. dry with materialthe combined organic phases were dried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-41b29fec1aa749cf8d6cc67f5df75098
Source dataset
uspto-grants-2016_07
Patent number
US09387203B2

Reaction notes

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